Becoming a Shemale Hooker: Chapter 3

Just as Mr. Jackson had instructed on the phone (in a hoarse and heavy-breathing voice), I pulled my car into the dark and mostly deserted office parking lot… and headed toward the illuminated place under the lamp-post. There I was to park — in the spotlight under the lamp-post. The phallic symbolism — I couldn’t help but smile — relieved at least some of my anxiety. My next instructions were these:

Turn the car engine off. Turn on the car’s inside lights. Look in the rear-view mirror and start touching up my makeup, specifically my lipstick. Wait for my cell to ring, which it now did just moments after I had deposited my lipliner back in my purse.

“Yes, Mr. Jackson…. Yes, Mr. Jackson…. Yes, of course, I want to make you happy.” After his abrupt goodbye, I proceeded to do exactly as I had just been told:

Make believe I’m just a normal businesswoman arriving at a real job. Open the car door. Stay seated, but swivel my legs so that my heels are on the pavement. Make sure that my skirt is hiked up, so that an observer from the office building can see my crotch.

“Wear no panties!” he had earlier commanded. Now I began to understand. And I followed precisely the rest of his instructions:

Pretend I’m unaware of either the observer or the fact that my crotch is showing. When I stand up, feint surprise that my skirt is hiked up so high; quickly tug it down to mid-thigh; look around, embarrassed, to make sure no one has seen me; then walk briskly, as if late for work, to the office entrance.

Buzzed through security, I then took the elevator to the second floor. There waiting for me as I exited the elevator was Mr. Jackson. I can’t describe exactly the man I had expected as my very first “John,” but he definitely wasn’t it! And his voice no longer made me tremble:

“You’re beautiful,” he said — the binoculars still in hand that he had obviously used to spy on me arriving in the parking lot. “The agency’s photos don’t do you justice.”

“Thank you, Mr. Jackson.”

“Just call me Jack,” he said, holding the door open for me to step into Suite 210.